Triphenylphosphine → HCID 18397192, compound

HRID 376773Notes

Reaction equation

HRID 376773 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:32][C:33]1[C:38]([F:39])=[C:37]([OH:40])[CH:36]=[CH:35][C:34]=1[C:41]1[N:46]=[CH:45][C:44]([C:47]2[CH:48]=[N:49][C:50]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])=[CH:51][CH:52]=2)=[CH:43][N:42]=1.[F:62][C@@H:63]([CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH2:64]O>C1COCC1>[F:32][C:33]1[C:38]([F:39])=[C:37]([O:40][CH2:64][C@@H:63]([F:62])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH:36]=[CH:35][C:34]=1[C:41]1[N:46]=[CH:45][C:44]([C:47]2[CH:48]=[N:49][C:50]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])=[CH:51][CH:52]=2)=[CH:43][N:42]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22857780HCID 22857780, compoundHCID 1355974452-(2,3-Difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine

Product 1

HCID 18397192HCID 18397192, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.2 mmol of diethyl azodicarboxylate are added dropwise at 0° C. to 3.2 mmol of triphenylphosphine in 20 ml of THF, and the mixture is stirred at room temperature for a further 20 minutes. 2.4 mmol of 2-(2,3-difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine and 2.4 mmol of 2-(S)-fluorodecanol are then added, and the reaction mixture is allowed to stand overnight. After the solvent has been removed in vacuo, the crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent and is recrystallized from acetonitrile, giving 1.2 g (86%) of colorless crystals, X 97 SC * 150.5 SA 161.5 I.

Workup

  1. waitto stand overnight
  2. customAfter the solvent has been removed in vacuo
  3. customthe crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent
  4. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-08b81b1a3c2d436a9ed3634aed1196ad
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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